European Journal of Organic Chemistry

Cover image for Vol. 2015 Issue 10

Early View (Online Version of Record published before inclusion in an issue)

Editor: Haymo Ross, Deputy Editor: Susan Wilkinson

Impact Factor: 3.154

ISI Journal Citation Reports © Ranking: 2013: 14/58 (Chemistry Organic)

Online ISSN: 1099-0690

Associated Title(s): Advanced Synthesis & Catalysis, Asian Journal of Organic Chemistry


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  1. Full Papers

    1. Fluorinated Compounds

      Difluoromethyl and Chlorofluoromethyl Sulfoximines: Synthesis and Evaluation as Electrophilic Perfluoroalkylating Reagents

      Bruce Pégot, Céline Urban, Aaron Bourne, Thanh Nghi Le, Sébastien Bouvet, Jérôme Marrot, Patrick Diter and Emmanuel Magnier

      Article first published online: 26 MAR 2015 | DOI: 10.1002/ejoc.201500201

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      Bromodifluoromethyl and dichlorofluoromethyl sulfoximines are transformed into the Hu electrophilic difluoromethylating reagent, and into a new chlorofluoromethylating reagent, respectively.

    2. Cascade Synthesis of Pyrroles

      Synthesis of Polysubstituted Pyrroles from Activated Alkynes and N-Propargylamines through Base-Catalyzed Cascade Reaction

      Jianquan Weng, Yong Chen, Binjie Yue, Meng Xu and Hongwei Jin

      Article first published online: 26 MAR 2015 | DOI: 10.1002/ejoc.201500166

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      An efficient method for the synthesis of polysubstituted pyrroles from activated alkynes and N-propargylamines has been developed. This cascade process represents an atom- and step-economical way to construct a range of polysubstituted pyrroles and involves base-catalyzed Michael addition/alkyne carbocyclization or Michael addition/aza-Claisen rearrangement/cyclization.

    3. Oligosaccharide Synthesis

      A Convergent Synthesis of 6-O-Branched β-Glucan Oligosaccharides

      Guochao Liao, Srinivas Burgula, Zhifang Zhou and Zhongwu Guo

      Article first published online: 24 MAR 2015 | DOI: 10.1002/ejoc.201500229

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      A highly convergent and efficient strategy relying on preactivation-based iterative glycosylation with thioglycosides as glycosyl donors was developed for the synthesis of 6-O-branched β-glucan oligosaccharides. The target molecules can be used for detailed structure–activity relationship studies of β-glucans, and for the design of β-glucan-based vaccines.

  2. Microreviews

    1. Azolylpurine Derivatives

      Synthesis and Applications of Azolylpurine and Azolylpurine Nucleoside Derivatives

      Irina Novosjolova, Ērika Bizdēna and Māris Turks

      Article first published online: 23 MAR 2015 | DOI: 10.1002/ejoc.201403527

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      This microreview describes different approaches for the synthesis of C(2)-, C(6)-, C(8)-, N(7)-, and N(9)-azolyl-substituted purine and purine nucleoside derivatives. Different methodologies including SNAr, cyclization, and transition-metal-catalyzed cross-coupling reactions are reviewed. These derivatives are important due to their wide applications in medicinal and biological chemistry.

  3. Full Papers

    1. Conjugated Diporphyrins

      Synthetic, Structural, and Spectroscopic Studies of Bis(porphyrinzinc) Complexes Linked by Two-Atom Conjugating Bridges

      Shannon R. Harper, Michael C. Pfrunder, Louisa J. Esdaile, Paul Jensen, John C. McMurtrie and Dennis P. Arnold

      Article first published online: 23 MAR 2015 | DOI: 10.1002/ejoc.201500183

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      A series of zinc(II) 5,10,15-triphenylporphyrin complexes linked at the meso positions through two-atom bridges (C2H2, C2, CH=N, and N2) is prepared. The UV/Vis spectra show split B bands, and the azoporphyrin clearly has the strongest ground-state inter-porphyrin interactions. The imine and especially the azo diporphyrins show strongly quenched fluorescence emission.

    2. Marine Natural Products

      Diterpenes with Unprecedented Skeletons from the Red Alga Sphaerococcus coronopifolius

      Vangelis Smyrniotopoulos, Robert Kiss, Véronique Mathieu, Constantinos Vagias and Vassilios Roussis

      Article first published online: 20 MAR 2015 | DOI: 10.1002/ejoc.201500133

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      Chemical investigation of the red alga Sphaerococcus coronopifolius led to the isolation and structure elucidation of the three new minor metabolites 13, featuring rearranged tricyclic diterpene skeletons. The in vitro antitumour activities of 13 were evaluated against one murine cancer cell line and five human cancer cell lines.

    3. Carbon-Sulfur Bond Formation

      Dithiooxamide as an Effective Sulfur Surrogate for Odorless High-Yielding Carbon­–Sulfur Bond Formation in Wet PEG200 as an Eco-Friendly, Safe, and Recoverable­ Solvent

      Habib Firouzabadi, Nasser Iranpoor, Forough Gorginpour and Arash Samadi

      Article first published online: 20 MAR 2015 | DOI: 10.1002/ejoc.201500156

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      Dithiooxamide has been employed as a sulfur surrogate for the generation of C–S bonds in high yields by using alkyl and aryl halides. This method was also used for the preparation of thia-Michael adducts in high yields. All of the reactions were performed in wet PEG200 (PEG = polyethylene glycol) under odorless conditions.

    4. Iminosugars

      Diastereoselective Overman Rearrangement of an L-Ascorbic-Acid-Derived Allylic Alcohol: Application in the Synthesis of (+)-1,2-Di-epi-swainsonine and a Tetrahydroxypyrrolizidine

      Parasuraman Rajasekaran, Alafia A. Ansari and Yashwant D. Vankar

      Article first published online: 20 MAR 2015 | DOI: 10.1002/ejoc.201500129

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      Syntheses of (+)-1,2-di-epi-swainsonine and a tetrahydroxypyrrolizidine are reported from an L-ascorbic-acid-derived allylic alcohol through a diastereoselective Overman rearrangement.

    5. Electrocyclic Reactions

      Interception of Nazarov Reactions of Allenyl Vinyl Ketones with Dienes: (3+2)- versus (4+3)-Cycloaddition and Subsequent Rearrangement

      Timothy D. R. Morgan, François M. LeFort, Zhe Li, Vanessa M. Marx, Russell J. Boyd and D. Jean Burnell

      Article first published online: 20 MAR 2015 | DOI: 10.1002/ejoc.201403618

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      The oxyallyl cation from the Lewis acid mediated Nazarov reaction of an allenyl vinyl ketone can be intercepted by cycloaddition with a diene. Depending on the substitution on the diene, the cycloaddition can be (4+3) (e.g., left) or (3+2) (e.g., center). Subsequent acid-mediated rearrangement of the latter product can lead to the formation of a larger ring (e.g., right).

  4. Microreviews

    1. Anion Receptors

      Recent Advancements in Calix[4]pyrrole-Based Anion-Receptor Chemistry

      Indrajit Saha, Jeong Tae Lee and Chang-Hee Lee

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejoc.201403701

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      Synthetic developments and anion-binding properties of newly developed calix[4]pyrroles are extensively discussed and accomplishments to date are summarized. Specifically, the formation of supramolecular organic frameworks and the possibility of customizing nanoscale structures through noncovalent interactions such as hydrogen bonding, anion–π interactions, and Coulombic interaction are addressed.

  5. Short Communications

    1. C–H Activation

      Palladium-Catalyzed Domino Mizoroki–Heck/Intermolecular C(sp3)–H Activation Sequence: An Approach to the Formation of C(sp3)–C(sp3) Bonds

      Wei Wang, Rong Zhou, Zhi-Jie Jiang, Xin Wang, Hai-Yan Fu, Xue-Li Zheng, Hua Chen and Rui-Xiang Li

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejoc.201500116

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      A palladium-catalyzed domino Mizoroki–Heck/intermolecular unactivated C(sp3)–H alkylation reaction is reported for the first time. This catalytic reaction provides an efficient method for the synthesis of dimeric dihydrobenzofurans from simple starting materials. This reaction provides a new method for the devising of domino reactions by including a C(sp3)–C(sp3) bond-forming reaction as a key step.

  6. Full Papers

    1. Condensed Ring Systems

      Reaction of Bicyclic Zirconacyclopentenes with Aldehydes and a Potential Pathway to Condensed 5–7–6(Ar) Ring Systems

      Nikola Topolovčan, Illia Panov and Martin Kotora

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejoc.201500248

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      The insertion of aldehydes into bicyclic zirconacyclopentenes mainly leads to oxazirconacycloheptenes. Subsequent hydrolysis or halogenolysis furnishes the corresponding alcohols or halides in moderate yields. The insertion of o-iodobenzaldehyde followed by intramolecular coupling in the presence of Cu and/or Pd compounds leads to the tricyclic condensed 5–7–6(aryl) ring system in reasonable yields.

  7. Microreviews

    1. Natural Product Synthesis

      Progress in the Preparation of Jatrophane Diterpenes

      Uwe Rinner

      Article first published online: 19 MAR 2015 | DOI: 10.1002/ejoc.201403598

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      Jatrophane diterpenes are fascinating natural products, obtained from species of the Euphorbiaceae plant family. The biosynthesis of Euphorbiaceae constituents as well as their biological properties are briefly outlined followed by a detailed discussion of syntheses and approaches to jatrophane diterpenes.

  8. Short Communications

    1. Heterocycle Synthesis

      Synthesis of 5-Iodo-4H-1,3-oxazine-4-ones Through a [3+3] Reaction of Amides and Propiolates Induced by N-Iodosuccinimide (NIS) and Cu(CF3SO3)2

      Chen Li, Nan Liu, Qing-Rong Qi, Yue Chen and Ling He

      Article first published online: 18 MAR 2015 | DOI: 10.1002/ejoc.201500015

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      A mild, one-pot procedure to access 5-iodo-4H-1,3-oxazine-4-ones has been developed. The reaction involves an N-iodosuccinimide and Cu(CF3SO3)2 induced [3+3] reaction of amides and propiolates. The products are formed in moderate to excellent yields and their further derivatization through cross-coupling reactions is reported.

  9. Full Papers

    1. Sulfonimidamides

      Cu(OAc)2-Catalysed Oxidative Dual C–H/N–H Activation of Terminal Alkynes and N-Deprotected Sulfonimidamides: An Easy Access to N-Alkynylated Sulfonimidamides

      Ganesh Chandra Nandi, Sudhakar Rao Kota, Tricia Naicker, Thavendran Govender, Hendrick G. Kruger and Per I. Arvidsson

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500239

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      N-Alkynylated sulfonimidamides have been synthesised through the CuII-catalysed N–H/C–H activation reaction of N-deprotected sulfonimidamides and terminal alkynes. The resulting N-alkynylated sulfonimidamides react with SiO2 or BH3·SMe2 to give the corresponding carbonyl or alkyl derivative, respectively.

    2. Natural Product Synthesis

      A Diels–Alder Approach to a Communesin Model: A/B-Cyclization Route

      Angelo Sanzone and Peter Somfai

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500177

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      Compound 3, a model system for communesin F, was approached by using a Diels–Alder reaction for the introduction of the vicinal quaternary stereocentres. All six rings were introduced, although it was not possible to achieve the required bis-aminal oxidation state.

    3. Natural Products

      Structure and Absolute Configuration of Auriculamide, a Natural Product from the Predatory Bacterium Herpetosiphon aurantiacus

      Sebastian Schieferdecker, Nicole Domin, Christine Hoffmeier, Donald A. Bryant, Martin Roth and Markus Nett

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500181

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      Chemical analysis of culture extracts from the predatory bacterium Herpetosiphon aurantiacus led to the discovery of the new natural product auriculamide, the structure of which was elucidated by MS and NMR analyses. The absolute configuration was determined, after hydrolysis, by chromatographic comparison with synthetic standards. A gene cluster for the biosynthesis of auriculamide is proposed.

    4. Cavitands

      Tribenzotriquinacene-Based Triscyclophanes: Intra- and Inter-Wing C3v-Symmetrical Extension of the Bowl-Shaped Tribenzotriquinacene Core

      Ehsan Ullah Mughal, Beate Neumann, Hans-Georg Stammler, Zhi-Min Li, Jun Wei, Dietmar Kuck and Xiaoping Cao

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500219

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      Highly concave tribenzotriquinacene-based cavitands were synthesized by efficient threefold incorporation of the respective para- and meta-dihydroxy- and -dimercaptobenzenes across the 3D-bays of the rigid, bowl-shaped tribenzotriquinacene core. Incorporation of the corresponding ortho-isomers afforded the respective threefold wing-extended isomers.

    5. Nitrene Transfer Reactions

      Sulfur Imidations by Light-Induced Ruthenium-Catalyzed Nitrene Transfer Reactions

      Vincent Bizet and Carsten Bolm

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500220

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      N-Acyl nitrenes have been generated from heterocyclic precursors and their use in light-initiated ruthenium-catalyzed sulfur imidations has been demonstrated. A range of heterocycles were tested, and 3-substituted 1,4,2-dioxazol-5-ones were identified as the most effective starting materials. Mechanistic investigations led to a reaction scheme that reflects a complex catalytic process.

  10. Short Communications

    1. Lanthanide Catalysis

      Toward the Synthesis of Muironolide A: Synthesis and Structure of Heteroleptic Lanthanide–Terpyridine Complexes with 2-Oxo Amides

      Kyle Young, Qing Xiao and Armen Zakarian

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500174

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      Crystallographic structural study of Ln(terpy)–β-oxo amide complexes relevant to the total synthesis of muironolide A by a catalytic IMDA reaction is described.

  11. Full Papers

    1. Ene Reaction

      A DFT Study of Inter- and Intramolecular Aryne Ene Reactions

      Patricia Pérez and Luis R. Domingo

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500139

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      Inter- and intramolecular aryne-ene reactions occur through a one-step mechanism via nearly asynchronous transition states, in which C–C bond formation is slightly more advanced than the hydrogen transfer process. Electron localisation function (ELF) topological analysis of the C1–C2 region of benzyne shows that the 1,2-pseudodiradical vinyl structure causes its high reactivity.

    2. Heteroglycoclusters

      Hetero-Click Conjugation of Oligonucleotides with Glycosides Using Bifunctional Phosphoramidites

      Albert Meyer, Mathieu Noël, Jean-Jacques Vasseur and François Morvan

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500165

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      Heteroglycoclusters were synthesized using orthogonal hetero-click reactions involving i) CuI azide alkyne cycloadditions (CuAAC) and thiolation of bromoacetamide groups or ii) two successive CuAACs.

    3. Covalent Organic Polygons

      The Dynamic Assembly of Covalent Organic Polygons: Finding the Optimal Balance of Solubility, Functionality, and Stability

      Merry K. Smith, Alexander R. Goldberg and Brian H. Northrop

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500170

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      Getting in and out of the library: Six phenanthrene-based bis(catechol) derivatives are reported and their ability to undergo dynamic covalent self-assembly with benzenediboronic acid is investigated. The influence of different solubilizing groups at the 9- and 10-positions of phenanthrene, the effects of greater or lesser π-surface area, and the influence of hydrophobic and protic solvents on the efficacy of self-assembly are each investigated.

    4. Heterocyclic Chemistry

      Synthesis of 3,5,5-Trisubstituted 4-Hydroxy-4H,5H-1,2,4-oxadiazoles through the Condensation of N-Hydroxyamidoximes and Ketones or Aldehydes

      Ning Liu, Lian-Jie Zhai, Peng Lian, Hui Li and Bo-Zhou Wang

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500083

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      A convenient method was developed for the synthesis of 3,5,5-trisubstituted 4-hydroxy-4H,5H-1,2,4-oxadiazole derivatives that proceeds through the condensation reaction of N-hydroxyamidoximes and ketones or aldehydes. These reactions were efficiently carried out at room temperature in the absence of a catalyst and afforded the corresponding products in excellent yields.

    5. Insight into O2-Promoted Base-Catalyzed N-Alkylation of Amines with Alcohols

      Chao Wang, Changpeng Chen, Jian Han, Jingyu Zhang, Yingming Yao and Yingsheng Zhao

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500086

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      A highly efficient and practical transition-metal-free CsOH/O2 catalyst system was developed for the N-alkylation of amines with alcohols under argon. This strategy has excellent functional group tolerance and is compatible with a wide scope of substrates. The mechanistic study revealed the necessity of a catalytic amount of O2 and the role of the base in the hydrogen autotransformation.

    6. Asymmetric Hydrogenation

      Pinene-Derived Monodentate Phosphoramidites for Asymmetric Hydrogenation

      Christian Schmitz, Walter Leitner and Giancarlo Franciò

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500120

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      A set of novel phosphoramidite ligands based on a pinene-derived chiral amine have been synthesized and evaluated in the rhodium-catalyzed asymmetric hydrogenation of functionalized olefins as well as in the iridium-catalyzed asymmetric hydrogenation of imines. Enantioselectivities of up to 99 (Rh) and 81 % ee (Ir) were achieved in these reactions.

    7. Ketones

      Modular Synthesis of Dihydroxyacetone Monoalkyl Ethers and Isosteric 1-Hydroxy-2-alkanones

      Deniz Güclü, Madhura Rale and Wolf-Dieter Fessner

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201403695

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      Terminal ketols are an important class of compounds for stereospecific enzymatic aldol additions and for the determination of the substrate promiscuity of enzymes. Herein, the straightforward scalable synthesis of two complementary substrate families is reported: ketols carrying alkylated ether moieties and their structurally complementary 1-hydroxyalkan-2-ones, starting from simple precursors.

    8. Fluorination

      Silver-Mediated Decarboxylative Fluorination of Paraconic Acids: A Direct Entry to β-Fluorinated γ-Butyrolactones

      Supasorn Phae-nok, Darunee Soorukram, Chutima Kuhakarn, Vichai Reutrakul and Manat Pohmakotr

      Article first published online: 17 MAR 2015 | DOI: 10.1002/ejoc.201500023

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      A strategy for the direct and site-selective incorporation of a fluorine atom at the β position of γ-butyrolactones is reported. Starting from stable and readily available paraconic acid derivatives, and using AgNO3 and commercially available Selectfluor® as a fluorine source, the reaction gives β-fluorinated γ-butyrolactones, useful precursors for organic synthesis and pharmaceutical chemistry.

  12. Short Communications

    1. Indole Synthesis

      A Copper-Mediated Oxidative Coupling Route to 3H- and 1H-Indoles from N-Aryl-enamines

      Pauline Drouhin and Richard J. K. Taylor

      Article first published online: 13 MAR 2015 | DOI: 10.1002/ejoc.201500112

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      An efficient copper-mediated oxidative coupling approach for the cyclisation of linear enamines to indole derivatives is described. The transformation can be efficiently carried out using inexpensive copper(II) salts.

  13. Full Papers

    1. Synthesis and DNA-Damaging Properties of Cisplatin-N-Mustard Conjugates

      Stefan Schiesser, Benjamin Hackner, Milan Vrabel, Wolfgang Beck and Thomas Carell

      Article first published online: 13 MAR 2015 | DOI: 10.1002/ejoc.201500144

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      Two cisplatin-N-mustard conjugates have been synthesized with the two cytotoxic groups separated by one or four ethylene glycol units. MS analyses of their reactions with DNA duplexes proved that both cytotoxic groups can bind to DNA, leading to a variety of DNA lesions that should hamper the repair machinery of tumor cells to counteract cisplatin resistance. Both conjugates inhibit cell division.

    2. Ritter Reaction

      Mechanochemical Ritter Reaction: A Rapid Approach to Functionalized Amides at Room Temperature

      Irena Dokli and Matija Gredičak

      Article first published online: 13 MAR 2015 | DOI: 10.1002/ejoc.201500051

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      Gentle Ritter: A fast and efficient mechanochemical Ritter reaction under mild conditions is described. The reaction proceeds rapidly at room temperature in a solvent-free or low-solvent environment by using sulfuric acid as catalyst.

    3. Arsine Ligand Design

      Bulky Monodentate Biphenylarsine Ligands: Synthesis and Evaluation of Their Structure Effects in the Palladium-Catalyzed Heck Reaction

      Gisela J. Quinteros, Paula M. Uberman and Sandra E. Martín

      Article first published online: 13 MAR 2015 | DOI: 10.1002/ejoc.201403658

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      Sterically demanding biphenyl-based arsine ligands were prepared in high overall yields by microwave-assisted Suzuki–Miyaura coupling. The ligands were evaluated in the Pd-catalyzed Heck coupling reaction; the most active were those with “blocked“ ortho-positions on the non-arsine-containing ring of the biphenyl backbone.

    4. Cycloaddition

      Diastereoselective Synthesis of Indolindiones by Formal [5+1] Double Michael Cycloaddition to 4-Cinnamoylpyrrolediones

      Pavel S. Silaichev, Valeriy O. Filimonov, Pavel A. Slepukhin, Michael Rubin and Andrey N. Maslivets

      Article first published online: 11 MAR 2015 | DOI: 10.1002/ejoc.201500141

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      An efficient [5+1] double Michael cycloaddition (DMCA) of enolates to 4-cinnamoylpyrrole-2,3-diones is demonstrated; the reaction allows for the highly diastereoselective assembly of indoline scaffolds with up to three contiguous stereogenic centers.

    5. Rare Sugar Synthesis

      Large-Scale Synthesis of Crystalline 1,2,3,4,6,7-Hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose

      Christian Stanetty and Ian R. Baxendale

      Article first published online: 10 MAR 2015 | DOI: 10.1002/ejoc.201500024

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      A practical synthesis of crystalline 1,2,3,4,6,7-hexa-O-acetyl-L-glycero-α-D-manno-heptopyranose in four simple steps from L-lyxose is disclosed. The process requires only two recrystallisations and was demonstrated on a >100 mmol scale, allowing rapid access to this important bacterial sugar building block in a convenient storage form.

    6. Natural Product Synthesis

      Studies towards the Leucetta-Derived Alkaloids Spirocalcaridine A and B – Possible Biosynthetic Implications

      Panduka B. Koswatta, Jayanta Das, Muhammed Yousufuddin and Carl J. Lovely

      Article first published online: 9 MAR 2015 | DOI: 10.1002/ejoc.201403650

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      A putative approach to the Leucetta-derived alkaloids predicated on the elaboration of spirofused cyclohexandienols is described. However, the strategy is compromised by rearrangement of key intermediates into corresponding naphthimidazole derivatives. This latter observation suggests a new hypothesis about the biosynthetic origins of this family of natural products.

    7. Synthetic Methods

      Copper-Catalyzed Direct Transformation of Secondary Allylic and Benzylic Alcohols into Azides and Amides: An Efficient Utility of Azide as a Nitrogen Source

      Balaji V. Rokade, Karthik Gadde and Kandikere Ramaiah Prabhu

      Article first published online: 9 MAR 2015 | DOI: 10.1002/ejoc.201500010

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      A mild and convenient method for the synthesis of amides has been explored by using secondary alcohols, Cu(ClO4)2·6H2O as a catalyst, and trimethylsilyl azide (TMSN3) as a nitrogen source in the presence of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) at ambient temperature. This method has also been adapted to the preparation of azides directly from their corresponding alcohols.

    8. Carbohydrates

      Base- and Radical-Mediated Regio- and Stereoselective Additions of Thiols, Thio-Sugars, and Thiol-Containing Peptides to Trisubstituted Activated exo-Glycals

      Mylène Richard, Claude Didierjean, Yves Chapleur and Nadia Pellegrini-Moïse

      Article first published online: 9 MAR 2015 | DOI: 10.1002/ejoc.201500130

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      The hydrothiolation of the trisubstituted double bond of push-pull exo-glycals was performed under radical and basic conditions. This addition reaction took place in a regio- and stereospecific manner and provided a strategy for the preparation of tertiary S-glycosides and complex neoglycopeptides of interest; EWG = electron-withdrawing group, P = protecting group, DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, and AIBN = azobis(isobutyronitrile).

  14. Short Communications

    1. Lactam Synthesis

      Reductive Cyclization and Petasis-Like Reaction for the Synthesis of Functionalized γ-Lactams

      Peng Wu, Michael Åxman Petersen, A. Emil Cohrt, Rico Petersen, Mads H. Clausen and Thomas E. Nielsen

      Article first published online: 9 MAR 2015 | DOI: 10.1002/ejoc.201500143

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      A novel approach to N-substituted β,γ-dihydroxy-γ-lactams through reductive cyclization and a Lewis acid mediated Petasis-like reaction to functionalized γ-lactams through nucleophilic addition of both electron-rich and electron-deficient boronic acids to N-acyliminium ions are disclosed.

  15. Full Papers

    1. Transport Manifolds

      Calixarene-Mediated Liquid Membrane Transport of Choline Conjugates 2: Transport of Drug-Choline Conjugates and Neurotransmitters

      Birendra Babu Adhikari, Sahar Roshandel, Ayu Fujii and Michael P. Schramm

      Article first published online: 9 MAR 2015 | DOI: 10.1002/ejoc.201403519

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      Ammonium species emerge as general and potent handles for effecting drug transport as mediated by ionizable calixarenes. Trimethylammonium, ammonium and ammonium carboxylates work in conjunction with phosphonic acid and carboxylic acid functionalized calix[n]arenes.

    2. Amination

      Palladium-Catalyzed Amination of Aryl Sulfides with Aliphatic Amines

      Ke Gao, Hideki Yorimitsu and Atsuhiro Osuka

      Article first published online: 6 MAR 2015 | DOI: 10.1002/ejoc.201500226

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      A palladium–NHC precatalyst shows high efficiency for C–S bond cleavage for the amination of aryl sulfides with aliphatic amines or aromatic amines.

    3. Samarium Diiodide Mediated Coupling of 2-Pyridylsulfonyl Furanosides with Aldehydes and Ketones: A General Synthesis of C-Furanosides

      Jin Wang, Fabien Gasc and Jacques Prandi

      Article first published online: 6 MAR 2015 | DOI: 10.1002/ejoc.201403640

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      C-Furanosides were obtained from the diiodosamarium-mediated coupling of anomeric 2-pyridyl sulfones derived from D-arabinose and D-ribose with aldehydes and ketones. Useful selectivities were observed and products with a trans relationship between the two carbon substituents on the tetrahydrofuran system were obtained.

    4. Bifunctional Organocatalysts

      Pyrimidine-Derived Prolinamides as Recoverable Bifunctional Organocatalysts for Enantioselective Inter- and Intramolecular Aldol Reactions under Solvent-Free Conditions

      Pascuala Vizcaíno-Milla, José M. Sansano, Carmen Nájera, Béla Fiser and Enrique Gómez-Bengoa

      Article first published online: 6 MAR 2015 | DOI: 10.1002/ejoc.201500007

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      The intermolecular ketone–aldehyde and aldehyde–aldehyde aldol reactions and the Hajos–Parrish–Eder–Sauer–Wiechert versions with the employment of chiral L-prolinamides containing the (R,R)- and (S,S)-trans-cyclohexane-1,2-diamine scaffold and a 2-pyrimidinyl unit are successfully performed under solvent-free conditions; WMK = Wieland–Miescher ketone.

    5. Isotopic Labelling

      Synthesis of a Panel of Carbon-13-Labelled (Glyco)Sphingolipids

      Patrick Wisse, Henrik Gold, Mina Mirzaian, Maria J. Ferraz, Ginger Lutteke, Richard J. B. H. N. van den Berg, Hans van den Elst, Johan Lugtenburg, Gijsbert A. van der Marel, Johannes M. F. G. Aerts, Jeroen D. C. Codée and Herman S. Overkleeft

      Article first published online: 6 MAR 2015 | DOI: 10.1002/ejoc.201500025

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      The synthesis of a focussed library of sphingolipids differing in the number and position of 13C labels is described. 13C atoms are incorporated into either the sphingosine or the palmitate moiety, or both. This set of compounds is intended for use in relative quantitative lipidomics studies to gain insight into sphingolipid metabolism.

    6. Conjugated Ferrocenes

      Reactions of Alkynyl- and 1,1′-Dialkynylferrocenes with Tetracyanoethylene – Unanticipated Addition at the Less Electron-Rich of Two Triple Bonds

      Nico Krauße, Marc Kielmann, Jingxiang Ma and Holger Butenschön

      Article first published online: 6 MAR 2015 | DOI: 10.1002/ejoc.201500105

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      The additions of tetracyanoethylene (TCNE) to alkynylferrocenes occur selectively at the most electron-rich triple bond. However, this broadly accepted rule is not obeyed when ferrocenium cations come into play.

  16. Short Communications

    1. Heterocycle Synthesis

      Solvent-Free Synthesis of 4H-Pyrido[1,2-a]pyrimidin-4-ones Catalyzed by BiCl3: A Green Route to a Privileged Backbone

      Irwan I. Roslan, Qiu-Xuan Lim, Aijuan Han, Gaik-Khuan Chuah and Stephan Jaenicke

      Article first published online: 5 MAR 2015 | DOI: 10.1002/ejoc.201500227

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      4H-Pyrido[1,2-a]pyrimidin-4-ones, a privileged backbone for developing drugs with good oral bioavailability, are easily synthesized by a solvent-free BiCl3-catalyzed tandem reaction with an expanded scope and excellent yields.

    2. P-Stereogenic Compounds

      Diastereoselective Hydrolysis of Asymmetric P–Cl Species and Synthesis of Optically Pure (RP)-(–)-Menthyl H-Phenylphosphinate

      Wei-Min Wang, Li-Juan Liu, Chang-Qiu Zhao and Li-Biao Han

      Article first published online: 5 MAR 2015 | DOI: 10.1002/ejoc.201500126

      Thumbnail image of graphical abstract

      Phenyl dichlorophosphine reacted with (L)-(–)-menthol to afford two diastereomers of menthyl phenylphosphinate (RP)-1a/(SP)-1a′ in up to 89:11 dr. Compound (RP)-1a was isolated in 58 % yield (60 g) and > 99:1 dr. An HCl-promoted diastereoselective hydrolysis of the P–Cl species was involved in the reaction. A mixture of 1a/1a′ with 50:50 dr was converted to a mixture enriched in 1a with 88:12 dr by treatment with phosphorus trichloride.

  17. Full Papers

    1. Fungal Constituents

      Tetrahydroanthraquinone Derivatives from the Endophytic Fungus Stemphylium globuliferum

      Yang Liu, Andreas Marmann, Mohamed S. Abdel-Aziz, Chang Yun Wang, Werner E. G. Müller, Wen Han Lin, Attila Mándi, Tibor Kurtán, Georgios Daletos and Peter Proksch

      Article first published online: 5 MAR 2015 | DOI: 10.1002/ejoc.201500079

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      Four tetrahydroanthraquinone derivatives 14 were obtained from the endophytic fungus Stemphylium globuliferum, which was isolated from Juncus acutus in Egypt. Their structures were determined by extensive NMR and electronic circular dichroism (ECD) spectroscopic analysis. The isolated compounds show IC50 values of 1.25 to 10.4 μM against the murine lymphoma cell line L5178Y.

    2. Design of Organocatalysts

      Remote Substituent Effects on the Stereoselectivity and Organocatalytic Activity of Densely Substituted Unnatural Proline Esters in Aldol Reactions

      María de Gracia Retamosa, Abel de Cózar, Mirian Sánchez, José I. Miranda, José M. Sansano, Luis M. Castelló, Carmen Nájera, Ana I. Jiménez, Francisco J. Sayago, Carlos Cativiela and Fernando P. Cossío

      Article first published online: 3 MAR 2015 | DOI: 10.1002/ejoc.201500160

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      Densely substituted enantiopure proline esters obtained through [3+2] cycloadditions catalyze aldol reactions. These synthetic organocatalysts produce different enantiomeric aldol adducts depending on the stereochemical dispositions of the substituents at distal positions with respect to the catalytic site. Design criteria are proposed for this kind of organocatalysts.

    3. Ligand Synthesis

      A Facile Route to Bis(pyridyl-1,3,5-triazine) Ligands with Fluorescing Properties

      Matthias F. Geist, Daniel Chartrand, Mihaela Cibian, Fabian Zieschang, Garry S. Hanan and Dirk G. Kurth

      Article first published online: 2 MAR 2015 | DOI: 10.1002/ejoc.201403521

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      Several bis(pyridyl-1,3,5-triazine) (dpt) ligands are prepared via Stille coupling with yields and scope of application superior to known trimerisation procedures. Ditopic ligands with different spacers are prepared and incorporation of p- and m-substituted phenyl rings enable access to different isomers. The absorption and emission properties can be tuned using oligothiophene spacers.

    4. Drug Synthesis

      A Stereoselective Catalytic Nitroaldol Reaction as the Key Step in a Strategy for the Synthesis of the Renin Inhibitor Aliskiren

      Sergio Rossi, Maurizio Benaglia, Riccardo Porta, Livius Cotarca, Paolo Maragni and Massimo Verzini

      Article first published online: 2 MAR 2015 | DOI: 10.1002/ejoc.201403659

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      A new strategy for a convergent synthesis of the first-in-class orally active direct renin inhibitor aliskiren has been developed.

    5. Fluorinated Compounds

      Synthesis of Trifluoromethyl-Containing Polysubstituted Aromatic Compounds by Diels–Alder Reaction of Ethyl 3-Benz­amido-2-oxo-6-(trifluoromethyl)-2H-pyran-5-carboxylate

      Ivan S. Kondratov, Nataliya A. Tolmachova, Violetta G. Dolovanyuk, Igor I. Gerus, Constantin-Gabriel Daniliuc and Günter Haufe

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500032

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      Reactions of ethyl 3-benzamido-2-oxo-6-(trifluoromethyl)-2H-pyran-5-carboxylate with cyclic alkenes and terminal acetylenes are useful for the efficient and selective preparation of trifluoromethyl-containing polyfunctionalised aromatic amino acid derivatives.

    6. Glycoside Synthesis

      A Practical Synthesis of Various 2-Deoxy-N-glycosides by Using D-Glucal

      Terence J. Meyerhoefer, Sonia Kershaw, Nadia Caliendo, Sumeia Eltayeb, Emi Hanawa-Romero, Polina Bykovskaya, Victor Huang, Cecilia H. Marzabadi and Michael De Castro

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500001

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      A series of 2-deoxy-2-iodo-N-glycosides were prepared by using D-glucal, N-iodosuccinimide, trimethylsilylacetamide, urea, imidazole, pyrrolidinone, and benzotriazole in good to excellent yields. Removal of iodine from C-2 of the newly generated 2-deoxy-2-iodo-N-glycosides led to formation of various 2-deoxy-N-glycosides.

    7. Substrate-Specific Cyclisation

      Preparation of Pyranose-Based Thioimidate N-Oxides (TINOs)

      Stéphanie Marquès, Marie Schuler and Arnaud Tatibouët

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201403619

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      Previously unknown pyranose-based thioimidate N-oxides (TINOs) were prepared by two strategies based on the cyclisation of suitably functionalised thiohydroximate functions anchored on various carbohydrate backbones, either through a Mitsunobu-type reaction or through desilylative cyclisation.

    8. Racemization

      Racemization of Olefinic Alcohols by a Carbonyl(cyclopentadienyl)ruthenium Complex: Inhibition by the Carbon–Carbon Double Bond

      Madeleine C. Warner and Jan-E. Bäckvall

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500066

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      Racemization of various sec-alcohol substrates containing a carbon–carbon double bond catalyzed by Ru(CO)25-C5Ph5)Cl was investigated. A strong inhibition of the rate of racemization was found for substrates having a C3–C5 chain with a terminal double bond. Alcohol substrates with a di- or trisubstituted double bond were found to give less inhibition of the racemization rate. The racemization reactions were studied by NMR spectroscopy with the aim of detecting intermediates.

    9. Dihydroxylations Revisited

      Asymmetric Dihydroxylation of Esters and Amides of Methacrylic, Tiglic, and Angelic Acid: No Exception to the Sharpless Mnemonic!

      Fabian Weber and Reinhard Brückner

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201403622

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      The Sharpless mnemonic is generally accepted as a predictive tool for the stereochemical outcome of Sharpless asymmetric dihydroxylation reactions. However, it was claimed that isobutyl tiglate is dihydroxylated with the opposite facial selectivity because of a preference for a “Chapleur transition state”. We have investigated this claim and proved it false.

    10. Annulated Heterocycles

      Carbonylative Synthesis of Phthalimides and Benzoxazinones by Using Phenyl Formate as a Carbon Monoxide Source

      Sujit P. Chavan and Bhalchandra M. Bhanage

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500109

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      A simple and efficient palladium-catalyzed carbonylative cyclization of N-substituted 2-iodobenzamides and 2-iodoanilides was investigated for the synthesis of phthalimides and benzoxazinones, respectively, by using phenyl formate as a CO source.

    11. Cross-Coupling

      Nucleophile-Selective Cross-Coupling Reactions with Vinyl and Alkynyl Bromides on a Dinucleophilic Aromatic Substrate

      Lu-Ying He, Mathias Schulz-Senft, Birk Thiedemann, Julian Linshoeft, Paul J. Gates and Anne Staubitz

      Article first published online: 27 FEB 2015 | DOI: 10.1002/ejoc.201500138

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      A nucleophile-selective one-pot cross-coupling reaction on an aromatic compound bearing both a stannyl group and a boronic ester has been developed with vinyl and alkynyl bromides as electrophiles, exploiting the different reactivity of the Stille and Suzuki–Miyaura cross-coupling reactions. The typical roles of the aromatic ring as the dielectrophile coupling to vinyl and alkynyl metal species are reversed, which presents a new tool for organic synthesis.

    12. Arene Hydrogenation

      Facile Arene Hydrogenation under Flow Conditions Catalyzed by Rhodium or Ruthenium on Carbon

      Tomohiro Hattori, Takashi Ida, Aya Tsubone, Yoshinari Sawama, Yasunari Monguchi and Hironao Sajiki

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejoc.201500050

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      A variety of aromatic compounds in iPrOH solution are readily hydrogenated to the corresponding saturated carbocyclic or heterocyclic compounds during a single pass of approximately 20 s through a catalyst cartridge packed with 10 % Rh/C or 10 % Ru/C together with hydrogen gas under relatively mild conditions.

    13. C–H Activation

      Palladium-Catalyzed C–H Bond Acylation of Acetanilides with Benzylic Alcohols under Aqueous Conditions

      Feihua Luo, Jun Yang, Zhengkai Li, Haifeng Xiang and Xiangge Zhou

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejoc.201500016

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      Palladium-catalyzed dehydrogenative coupling reactions between acetanilides and benzylic alcohols under aqueous conditions are reported. A wide range of benzophenone derivatives could be obtained in good to excellent yields up to 98 %. Mechanism studies showed that a bimetallic palladium cyclopalladated complex might be involved in the catalysis.

    14. Bioactive Neolignans

      A Diastereoselective Route to trans-2-Aryl-2,3-dihydrobenzofurans through Sequential Cross-Metathesis/Isomerization/Allylboration Reactions: Synthesis of Bioactive Neolignans

      Rémy Hemelaere, François Carreaux and Bertrand Carboni

      Article first published online: 25 FEB 2015 | DOI: 10.1002/ejoc.201500019

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      The development of a highly diastereoselective synthesis of trans-2,3-dihydrobenzofurans based on a cross-metathesis/isomerization/allylboration sequence is reported. This new approach was efficiently employed for the preparation of natural neolignans.

    15. Nitrogen Heterocycles

      Synthetic Route to Rare Isoindolones Derivatives

      Killian Oukoloff, Frédéric Buron, Sylvain Routier, Ludovic Jean and Pierre-Yves Renard

      Article first published online: 23 FEB 2015 | DOI: 10.1002/ejoc.201403649

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      A shorter and more versatile synthetic route has been developed to prepare tetrahydropyrido[2,1-a]isoindolone and superior analogues. The key step of this synthesis is the formation of the lactam ring by a cyclization using Shibasaki's conditions.

    16. Chiral Ionic Liquids

      Coordinating Chiral Ionic Liquids: Design, Synthesis, and Application in Asymmetric Transfer Hydrogenation under Aqueous Conditions

      Maria Vasiloiu, Peter Gaertner, Ronald Zirbs and Katharina Bica

      Article first published online: 20 FEB 2015 | DOI: 10.1002/ejoc.201403555

      Thumbnail image of graphical abstract

      The ruthenium-catalyzed asymmetric transfer hydrogenation of aromatic ketones was carried out under aqueous conditions by using a hydrophilic chiral ionic liquids with an amino alcohol substructure as the sole source of chirality. When used in the reaction system, these chiral ionic liquids provided high yields and excellent selectivities.

    17. 1,3-Dienes

      General Preparation of 1-Substituted (E)-1,3-Dienes under Mild Conditions

      Raquel G. Soengas, Humberto Rodríguez-Solla, Ainhoa Díaz-Pardo, Rita Acúrcio, Carmen Concellón, Vicente del Amo and Artur M. S. Silva

      Article first published online: 20 FEB 2015 | DOI: 10.1002/ejoc.201403623

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      A mild, straightforward and simple method to obtain 1-substituted (E)-1,3-dienes from very diverse functionalized aldehydes is reported. The procedure is based on the metal-promoted reductive β-elimination of 2-chloroallyl acetates, derived from aldehydes. Both In/CuI and Mg/ZnCl2 efficiently gave the dienes in good yields and with good to high stereoselectivities.

    18. Tandem Reactions

      Lewis-Acid-Catalysed Tandem Meinwald Rearrangement/Intermolecular [3+2]-Cycloaddition of Epoxides with Donor–Acceptor Cyclopropanes: Synthesis of Functionalized Tetrahydrofurans

      Ashok Kumar Pandey, Asit Ghosh and Prabal Banerjee

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403590

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      A Lewis-acid-catalysed tandem Meinwald rearrangement/[3+2]-cycloaddition of epoxides with donor–acceptor cyclopropanes to synthesize varieties of cis-2,5-aryl-benzyl-substituted tetrahydrofurans is described. An enantioselective version of the same transformation is also presented using various BOX ligands.

    19. Solid-State Halogenation

      Trihaloisocyanuric Acids as Atom-Economic Reagents for Halogenation of Aromatics and Carbonyl Compounds in the Solid State by Ball Milling

      Abhaya K. Mishra, Honnappa Nagarajaiah and Jarugu Narasimha Moorthy

      Article first published online: 19 FEB 2015 | DOI: 10.1002/ejoc.201403463

      Thumbnail image of graphical abstract

      Trihaloisocyanuric acids are shown to serve as excellent reagents for the facile, solvent-free halogenation of aromatics and carbonyl compounds under ball-milling conditions at room temperature.

    20. Conjugated Systems

      Swivel-Cruciform Stilbenes Based on Bithiophene

      Amaranda García-Rodríguez, Antonio M. Rodríguez, Pilar Prieto, Raquel Andreu, Sonia Merino and Julián Rodríguez-López

      Article first published online: 17 FEB 2015 | DOI: 10.1002/ejoc.201500071

      Thumbnail image of graphical abstract

      Bithiophene-based cruciforms with stilbenoid arms at the 3,3′- and 5,5′-positions adopt a twisted geometry owing to steric hindrance between the stilbene arms. This results in weaker intermolecular interactions and better solubility in common solvents. Electrochemical results demonstrate that these systems can support radical cations and show their potential as hole-transporting materials.

    21. Peptides

      Stabilization of a Natural β-Hairpin by a Twist-Compatible β-Turn Mimetic

      Matthias Körling and Armin Geyer

      Article first published online: 13 FEB 2015 | DOI: 10.1002/ejoc.201500048

      Thumbnail image of graphical abstract

      β-Hairpins detached from their natural protein environment usually lose their well-defined shape, although they fulfill all requirements to fold into a highly twisted hairpin peptide. In this study, two stabilization strategies from either end of the antiparallel β-strands, which reconstitute the shape of the discrete hairpin, are opposed to each other. The twist compatible β-turn mimetic Hot=Tap is shown to be superior to macrocyclic disulfides.

    22. Total Synthesis

      Isolation and Asymmetric Total Synthesis of Fungal Secondary Metabolite Hygrophorone B12

      Eileen Bette, Alexander Otto, Tobias Dräger, Kurt Merzweiler, Norbert Arnold, Ludger Wessjohann and Bernhard Westermann

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejoc.201403455

      Thumbnail image of graphical abstract

      Hygrophorone B12 was isolated from the fruiting bodies of Hygrophorus abieticola, and was synthesized in enantiomerically pure form using a Sharpless asymmetric dihydroxylation and two diastereoselective aldol-type reactions as the key steps. This approach enabled the unambiguous determination of the relative and absolute configuration of hygrophorones B for the first time.

    23. Natural Product Synthesis

      Synthesis of Simplified Halogenated Chondramide Derivatives with Strong Cytostatic Properties

      Dominic Becker and Uli Kazmaier

      Article first published online: 9 FEB 2015 | DOI: 10.1002/ejoc.201403577

      Thumbnail image of graphical abstract

      Easily available dichlorinated Chondramide derivatives show high antitumor-activity towards selected cancer cell lines.

  18. Microreviews

    1. Difunctionalization of Alkynes

      Direct Vicinal Difunctionalization of Alkynes: An Efficient Approach Towards the Synthesis of Highly Functionalized Fluorinated Alkenes

      Tatiana Besset, Thomas Poisson and Xavier Pannecoucke

      Article first published online: 5 FEB 2015 | DOI: 10.1002/ejoc.201403507

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      The concomitant introduction of fluorinated groups and an additional functional group into alkynes has attracted considerable attention as an efficient synthetic route towards polyfunctionalized fluorinated olefins. This microreview focuses on the major progress achieved in this field involving transition-metal-catalyzed transformations and radical processes.

    2. Synthesis of Azaheterocycles

      Furan's Gambit: Electrophile-Attack-Triggered Sacrifice of Furan Rings for the Intramolecular Construction of Azaheterocycles

      Igor V. Trushkov, Maxim G. Uchuskin and Alexander V. Butin

      Article first published online: 3 FEB 2015 | DOI: 10.1002/ejoc.201403580

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      Chemistry is like chess! A gambit is a chess opening in which a player sacrifices something to achieve something else. The concept of the gambit is also used in organic chemistry. This review deals with intramolecular transformations pertaining to the sacrifice of a furan ring for the production of a variety of nitrogen heterocycles.

    3. Green Chemistry

      Chitosan: An Upgraded Polysaccharide Waste for Organocatalysis

      Olivier Mahé, Jean-François Brière and Isabelle Dez

      Article first published online: 29 JAN 2015 | DOI: 10.1002/ejoc.201403396

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      This microreview outlines recent advances in achiral to asymmetric organocatalytic reactions based on chitosan, a biodegradable chiral polysaccharide obtained from marine wastes, in a sustainable chemistry context. The use of chitosan and its derivatives either as insoluble organocatalysts or as supports for organocatalysts is reviewed, together with shaping and reusability issues.

    4. Furopyridines

      Elaboration of Furopyridine Scaffolds

      Adeline Jasselin-Hinschberger, Corinne Comoy, Anthony Chartoire and Yves Fort

      Article first published online: 22 JAN 2015 | DOI: 10.1002/ejoc.201403412

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      This review is focused on furopyridines and especially on the different strategies that allow their synthesis.


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